ALDEHYDES, KETONES & CARBOXYLIC ACIDS PYQ & Solutions-1

ALDEHYDES, KETONES AND CARBOXYLIC ACIDS
1. Nucleophilic addition of Grignard reagent to ketones followed by hydrolysis

with dilute acids forms:
(A) Alkene (B) Primary alcohol (C) Tertiary alcohol (D)Secondary alcohol
2. Aspirin is formed by the acetylation of:
(A) Benzoic acid (B) Phenol (C) Salicylic acid (D) Phthalic acid
3. Rosenmund reduction is used for the preparation of Aldehydes.
The catalyst used in this reaction is
(A) Pd -BaSO4 (B) Anhydrous AlCI3 (C) Iron (Ill) oxide (D) HgS04
4. How will you bring about the following conversions? (any three)
(a) Ethanal to Propanone
(b) Acetophenone to Benzoic acid
(c) Bromobenzene to 1-Phenylethanol
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5. Give reasons for the following:
(1) In semi carbazide, only one NH2 group is involved in the formation of semi
carbazone.
Yes, only one NH2 group in semicarbazide is involved in the formation of
semicarbazone because the other NH2 group is involved in resonance and can't
participate
(2) Acetaldehyde is more reactive than acetone towards addition of HCN.
Yes, acetaldehyde is more reactive than acetone towards addition of HCN because
of steric and electronic factors:
• Steric hindrance
Acetaldehyde has less steric hindrance than acetone, making it easier for
nucleophiles to attack the carbonyl carbon
6. Name the reagent in the following reaction:
CH3CH = CH CH2CN ⎯⎯→ CH3CH = CHCH2CHO
Dibal-H (Di-isobutyl aluminum hydride)
7. Write the reaction involved in Hell-Volhard-Zelinsky reaction.
Carboxylic acids having an α-hydrogen are halogenated at the α-position on
treatment with chlorine or bromine in the presence of small amount of red
phosphorus to give α-halocarboxylic acids. The reaction is known as Hell-Volhard-
Zelinsky reaction.
8. a) An organic compound (A) with the molecular formula C9H10O forms 2, 4-

DNP derivative, reduces Tollen’s reagent and undergoes Cannizzaro reaction.
On vigorous oxidation, it gives 1, 2-benzene dicarboxylic acid.
(i) Identify the compound (A) and write its IUPAC name.
(ii) Write the reaction of compound (A) with
(1) 2, 4 - Dinitrophenyl hydrazine and (2) Tollens reagent
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(iii) Write the equation of compound (A) when it undergoes Cannizzaro
reaction.
An organic compound with the molecular formula C9H10O forms 2,4-DNP
derivative and also reduces Tollens reagent. Hence, the compound is an aldehyde.
The compound undergoes Cannizzaro reaction. Hence, it does not contain an alpha
H atom.
On vigorous oxidation, it gives 1,2-benzenedicarboxylic acid. Hence, -CHO group
is directly attached to benzene ring and the compound is ortho di-substituted
benzene.
(i) The compound (A) is 2-ethylbenzaldehyde.
(ii)
(iii)
9. Account for the following.

(1) The alpha (α)-hydrogens of aldehydes and ketones are acidic in nature.
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Yes, the alpha (α)-hydrogens of aldehydes and ketones are acidic in nature:
• Explanation
The carbonyl group of aldehydes and ketones has a strong electron-withdrawing
effect, which makes it easier to lose the α-hydrogen atoms in basic conditions. The
conjugate base that's formed after removing the α-hydrogen atom is stabilized by
resonance, which makes it easier to lose the α-hydrogen atoms.
(2) Oxidation of aldehydes is easier than ketones.
Yes, aldehydes are easier to oxidize than ketones:
• Aldehydes
Aldehydes are easily oxidized because they have a hydrogen atom attached to the
carbonyl carbon, which can be abstracted. This makes aldehydes strong reducing
agents that can be oxidized by many different oxidizing agents.
• Ketones
Ketones are generally resistant to oxidation because they don't have the hydrogen
atom attached to the carbonyl carbon. Ketones can only be oxidized under extreme
conditions, such as by very strong oxidizing agents like potassium permanganate
solution. However, these agents break carbon-carbon bonds in a destructive way.
10. Arrange the following in the order mentioned:
(1) Decreasing reactivity towards nucleophilic addition reaction propanal, acetone,
benzaldehyde.
Propanal  Acetone Benzaldehyde.
(2) Increasing order of boiling point: Propane Dimethyl ether Propanal Ethanol
Propane < Dimethyl ether < Propanal < Ethanol.
11. Give simple chemical test to distinguish between Benzoic acid and
Benzaldehyde.
Here are two chemical tests that can be used to distinguish between benzaldehyde
and benzoic acid:
• Sodium bicarbonate test
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Benzoic acid is an acid, so it reacts with sodium bicarbonate to form a sodium salt
and release carbon dioxide gas. B enzaldehyde does not react with sodium
bicarbonate.
• Tollen's reagent test
Also known as the silver mirror test, benzaldehyde reacts with ammoniacal silver
nitrate to produce a silver mirror, while benzoic acid produces a white precipitate
12. Write the reactions involved in the following:
(a) Wolff-Kishner reduction
(b) Decarboxylation reaction

Carboxylic acids lose carbon dioxide to form hydrocarbons when their sodium salts
are heated with sodalime (NaOH and CaO in the ratio of 3 : 1). The reaction is known
as decarboxylation.
(c) Cannizzaro reaction

Aldehydes which do not have an α-hydrogen atom, undergo self-oxidation and
reduction (disproportionation) reaction on heating with concentrated alkali. In this
reaction, one molecule of the aldehyde is reduced to alcohol while another is
oxidized to carboxylic acid salt.
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13. Explain why:
(i) Carboxyl group in benzoic acid is meta directing.
The carboxyl group in benzoic acid is meta directing because it withdraws electrons
from the benzene ring, making the meta position richer in electron density than the
ortho and para positions.
(ii) Sodium bisulphite is used for the purification of aldehydes and ketones.
Sodium bisulfite is used to purify aldehydes and ketones because it reacts with them
to form white crystalline precipitates that can be filtered out, removing impurities.
(iii) Carboxylic acids do not give characteristic reactions of carbonyl group.
Carboxylic acids do not give the characteristic reactions of carbonyl groups
because the carbonyl group in carboxylic acids is involved in resonance, making the
carbon atom less electrophilic.
14. (i) Carry out the following conversions:
(1) Ethanal to But-2-en-1-al
(2) Propanoic acid to 2-chloropropanoic acid
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(ii) An alkene with molecular formula C5H10 on ozonolysis gives a mixture of
two compounds B and C. Compound B gives positive Fehling test and also
reacts with iodine and NaOH solution. Compound ‘C’ doesn’t give Fehling
solution test but forms Iodoform. Identify the compounds A, B and C.
(i) Compound ′B′ gives Fehling's test that means it is aldehyde also it forms
iodoform so, compound B is acetaldehyde, among aldehydes.
(ii) (ii) Compound C does not give Fehling's test but forms iodoform so it must
be ketone having methyl group attached to carbonyl. Reactions are given
in the diagram.
15. Arrange the following compounds in order of property indicated: -

1. FCH2COOH, O2N-CH2-COOH, CH3COOH, HCOOH (in decreasing order of
acid character)
CH3COOH < HCOOH < FCH2COOH < O2N-CH2-COOH
2. Acetone, Acetaldehyde, Benzaldehyde, Acetophenone (in increasing order of
reactivity towards addition of HCN)
Acetophenone < Benzaldehyde < Acetone < Acetaldehyde
3. CH3CHO, CH3CH2OH, CH3OCH3, CH3CH2CH3 (in increasing order of boiling
point)
CH3CH2CH3  CH3CHO  CH3OCH3 CH3CH2OH
4. (CH3)2CHCOOH, CH3CH2CH(Br)COOH, CH3CH(Br)CH2COOH (in increasing
order of acid strength)
(CH3)2CHCOOH  CH3CH(Br)CH2COOH  CH3CH2CH(Br)COOH
5. Benzoic acid, 4-Nitrobenzoic acid, 3,4-Dinitrobenzoic acid, 4-Methoxybenzoic
acid (in increasing order of acid strength)
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4-methoxybenzoic acid  Benzoic acid  4-Nitrobenzoic acid  3,4-Dinitrobenzoic acid.
6. Ethanal, Propanal, Propanone, Butanone (in increasing order of reactivity towards

nucleophilic addition reaction)
Butanone  propanone  propanal  ethanal.
7. Benzaldehyde, p-Tolualdehyde, p-Nitrobenzaldehyde, Acetophenone (in
increasing order of reactivity towards nucleophilic addition reaction)
Acetophenone  p-tolualdehyde  benzaldehyde  p-nitrobenzaldehyde
8. CH3COOCH3, CH3COCl, CH3CONH2, (CH3CO)2O (in increasing order of
reactivity towards hydrolysis
CH3CONH2  CH3COOCH3  (CH3CO)2O  CH3COCl
16. How will you convert?
i) Ethyl benzene to benzoic acid.
ii) Acetophenone to benzoic acid.
iii) Bromobenzene to benzoic acid
iv) Phenylethene (styrene) to benzoic acid.
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17. How will you bring about the following conversions in not more than two
steps?
i) Propanone to Propene
Reduce propanone to propan-2-ol
CH3COCH3 + LiAlH4 → CH3CHOHCH3
Dehydrate propan-2-ol to propene
𝐻𝑒𝑎𝑡
CH3CHOHCH3 + H2SO4 → CH3CH=CH2 + H2O
(ii) Benzoic acid to Benzaldehyde

Benzoic acid can be converted to benzaldehyde through a two-step process that
involves chlorination and reduction
(iii) Ethanol to 3-Hydroxybutanal
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(iv) Benzene to m-Nitro acetophenone
(v) Benzaldehyde to Benzophenone
10 | P a g e

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ALDEHYDES, KETONES AND CARBOXYLIC ACIDS

1. Nucleophilic addition of Grignard reagent to ketones followed by hydrolysis

(b) Acetophenone to Benzoic acid

(c) Bromobenzene to 1-Phenylethanol

8. a) An organic compound (A) with the molecular formula C9H10O forms 2, 4-

9. Account for the following.

(b) Decarboxylation reaction

(c) Cannizzaro reaction

(2) Propanoic acid to 2-chloropropanoic acid

15. Arrange the following compounds in order of property indicated: -

6. Ethanal, Propanal, Propanone, Butanone (in increasing order of reactivity towards

ii) Acetophenone to benzoic acid.

iii) Bromobenzene to benzoic acid

iv) Phenylethene (styrene) to benzoic acid.

(ii) Benzoic acid to Benzaldehyde

(iii) Ethanol to 3-Hydroxybutanal

(v) Benzaldehyde to Benzophenone

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